1-Phenethylamine, (-)- → HCID 69068798, compound

HRID 1785461Notes

Reaction equation

HRID 1785461 reaction equation
[C:1]([Si:5]([CH3:35])([CH3:34])[O:6][CH:7]1[CH2:23][N:11]2[C:12](=[O:22])[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=[C:10]2[N:9]([C:24]2[CH:29]=[CH:28][N:27]=[C:26](S(C)(=O)=O)[N:25]=2)[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[C:36]1([C@@H:42]([NH2:44])[CH3:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O1CCOCC1.CCOC(C)=O>[C:1]([Si:5]([CH3:35])([CH3:34])[O:6][CH:7]1[CH2:23][N:11]2[C:12](=[O:22])[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=[C:10]2[N:9]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:44][CH:42]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH3:43])[N:25]=2)[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 57593167HCID 57593167, compound

Product 1

HCID 69068798HCID 69068798, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 7-(tert-butyl-dimethyl-silanyloxy)-9-(2-methanesulfonyl-pyrimidin-4-yl)-2-phenyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one, prepared from last step (0.6 mmol) and (S)-1-phenylethylamine (1.0 mL, 7.8 mmol) in dioxane (6 mL) was heated at 110° C. for 17 h. The brown solution was cooled to room temperature and was diluted with EtOAc (10 ML). The mixture was washed with H2O (2×), dried (Na2SO4), and concentrated to oil. Purification on silica (0-1% 2N NH3-MeOH in DCM) provided the product as a white solid. M+1: 555.

Workup

  1. temperatureThe brown solution was cooled to room temperature
  2. washThe mixture was washed with H2O (2×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to oil
  5. customPurification on silica (0-1% 2N NH3-MeOH in DCM)

Sources & evidence

ORD record
ord-764a1ae4db054e5ea156281aaf351f1a
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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